Details of the Drug

General Information of Drug (ID: DMNLQHK)

Drug Name
Tanespimycin
Synonyms
CNF-101; [(3S,5S,6R,7S,8E,10R,11S,12E,14E)-6-Hydroxy-5,11-dimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-21-(prop-2-enylamino)-17-azabicyclo[16.3.1]docosa-8,12,14,18,21-pentaen-10-yl] carbamate; [(3R,5S,6R,7S,8E,10S,11S,12Z,14E)-6-hydroxy-5,11-dimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-21-(prop-2-enylamino)-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] carbamate; 17AAG, Tanespimycin, Geldanamycin, NSC330507, 17-(Allylamino)-17-demethoxygeldanamycin, CP 127374
Indication
Disease Entry ICD 11 Status REF
Breast cancer 2C60-2C65 Phase 2 [1]
Multiple myeloma 2A83 Discontinued in Phase 3 [1]
Therapeutic Class
Anticancer Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 585.7
Logarithm of the Partition Coefficient (xlogp) 2.6
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 9
Chemical Identifiers
Formula
C31H43N3O8
IUPAC Name
[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-19-(prop-2-enylamino)-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl] carbamate
Canonical SMILES
C[C@H]1C[C@@H]([C@@H]([C@H](/C=C(/[C@@H]([C@H](/C=C\\C=C(\\C(=O)NC2=CC(=O)C(=C(C1)C2=O)NCC=C)/C)OC)OC(=O)N)\\C)C)O)OC
InChI
InChI=1S/C31H43N3O8/c1-8-12-33-26-21-13-17(2)14-25(41-7)27(36)19(4)15-20(5)29(42-31(32)39)24(40-6)11-9-10-18(3)30(38)34-22(28(21)37)16-23(26)35/h8-11,15-17,19,24-25,27,29,33,36H,1,12-14H2,2-7H3,(H2,32,39)(H,34,38)/b11-9-,18-10+,20-15+/t17-,19+,24+,25+,27-,29+/m1/s1
InChIKey
AYUNIORJHRXIBJ-TXHRRWQRSA-N
Cross-matching ID
PubChem CID
6505803
ChEBI ID
CHEBI:64153
CAS Number
75747-14-7
DrugBank ID
DB05134
TTD ID
D0SC2J
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Heat shock protein 90 alpha (HSP90A) TT78R5H HS90A_HUMAN Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
3-hydroxyacyl-CoA dehydrogenase type-2 (HSD17B10) OT7RJON4 HCD2_HUMAN Gene/Protein Processing [3]
A disintegrin and metalloproteinase with thrombospondin motifs 1 (ADAMTS1) OTTLJH8W ATS1_HUMAN Gene/Protein Processing [4]
Albumin (ALB) OTVMM513 ALBU_HUMAN Drug Response [5]
ALK tyrosine kinase receptor (ALK) OTV3P4V8 ALK_HUMAN Gene/Protein Processing [6]
Alpha-enolase (ENO1) OTB1KWJS ENOA_HUMAN Gene/Protein Processing [3]
Androgen receptor (AR) OTUBKAZZ ANDR_HUMAN Gene/Protein Processing [7]
Annexin A1 (ANXA1) OT5OFDJC ANXA1_HUMAN Gene/Protein Processing [3]
Anterior gradient protein 2 homolog (AGR2) OTRRZT7W AGR2_HUMAN Gene/Protein Processing [3]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [8]
Apoptotic protease-activating factor 1 (APAF1) OTJWIVY0 APAF_HUMAN Gene/Protein Processing [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

ICD Disease Classification 02 Neoplasm
Disease Class ICD-11: 2C82 Prostate cancer
The Studied Tissue Bone marrow
The Studied Disease Multiple myeloma [ICD-11:2C82]
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Heat shock protein 90 alpha (HSP90A) DTT HSP90AA1 5.98E-06 1.3 4.35
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7751).
2 Tanespimycin: the opportunities and challenges of targeting heat shock protein 90. Expert Opin Investig Drugs. 2009 Jun;18(6):861-8.
3 Impact of Heat Shock Protein 90 Inhibition on the Proteomic Profile of Lung Adenocarcinoma as Measured by Two-Dimensional Electrophoresis Coupled with Mass Spectrometry. Cells. 2019 Jul 31;8(8):806. doi: 10.3390/cells8080806.
4 Candidate therapeutic agents for hepatocellular cancer can be identified from phenotype-associated gene expression signatures. Cancer. 2009 Aug 15;115(16):3738-48. doi: 10.1002/cncr.24417.
5 Stability of the Hsp90 inhibitor 17AAG hydroquinone and prevention of metal-catalyzed oxidation. J Pharm Sci. 2008 Dec;97(12):5147-57. doi: 10.1002/jps.21394.
6 The neuroblastoma-associated F1174L ALK mutation causes resistance to an ALK kinase inhibitor in ALK-translocated cancers. Cancer Res. 2010 Dec 15;70(24):10038-43. doi: 10.1158/0008-5472.CAN-10-2956. Epub 2010 Oct 28.
7 Gene expression signature-based chemical genomic prediction identifies a novel class of HSP90 pathway modulators. Cancer Cell. 2006 Oct;10(4):321-30.
8 Analysis of expression of heat shock protein-90 (HSP90) and the effects of HSP90 inhibitor (17-AAG) in multiple myeloma. Leuk Lymphoma. 2006 Jul;47(7):1369-78. doi: 10.1080/10428190500472123.
9 Apoptosis induction in human leukemic cells by a novel protein Bengalin, isolated from Indian black scorpion venom: through mitochondrial pathway and inhibition of heat shock proteins. Chem Biol Interact. 2010 Jan 27;183(2):293-303. doi: 10.1016/j.cbi.2009.11.006. Epub 2009 Nov 12.